Ligands for production of 1-octene in chromium assisted ethylene oligomerization process

Patent metadata

Field	Value
Publication number	US-12440830-B2
Application number	US-202017435831-A
Country	US
Kind code	B2
Filing date	Mar 16, 2020
Priority date	Mar 19, 2019
Publication date	Oct 14, 2025
Grant date	Oct 14, 2025

Abstract

Processes to produce tunable mixtures of 1-hexene and 1-octene are described. The process includes contacting a mixture of a 1-hexene catalyst and a 1-octene catalyst with ethylene under conditions sufficient to produce a composition that includes a desired amount 1-hexene and 1-octene are described.

First claim

The invention claimed is:

1. A catalyst composition for the production of 1-hexene and 1-octene, the catalyst composition comprising a 1-hexene catalyst and a 1-octene catalyst, wherein the 1-hexene catalyst and the 1-octene catalyst comprise a nitrogen, phosphorous, nitrogen, phosphorous, nitrogen (NPNPN) ligand, and wherein the 1-hexene catalyst comprises a ligand having a structure of:

where R 1 and R 2 are the same or different and are selected from the group consisting of (i) C 3 to C 4 non-cyclic aliphatic groups, (ii) C 5 to C 10 aliphatic groups which may be cyclic or non-cyclic, linear or branched, substituted or unsubstituted, and (iii) any combination thereof, and wherein n is 0 or 1, and m=n+3.

2. The catalyst composition of claim 1 , wherein catalyst composition further comprises:
a chromium (III) species; and
an activator or co-catalyst.

3. The catalyst composition of claim 1 , wherein the 1-octene catalyst comprises a ligand having a structure of:

where Ar 1 and Ar 2 are each independently an aromatic group or a substituted aromatic group, n is 0 or 1 and m=n+3.

4. The catalyst composition of claim 3 , wherein the Ar 1 and Ar 2 are each independently a phenyl group or an alkyl substituted phenyl group.

5. The catalyst composition of claim 4 , wherein the ligand of the 1-octene catalyst has the structure of:

6. The catalyst composition of claim 4 , wherein the ligand of the 1-octene catalyst has the structure of:

7. The catalyst composition of claim 1 , wherein R 1 and R 2 are each independently a C 5 to C 10 cyclic hydrocarbon group or a substituted C 5 to C 10 cyclic hydrocarbon group.

8. The catalyst composition of claim 7 , wherein the 1-hexene ligand has the structure of:

9. The catalyst composition of claim 7 , wherein the 1-hexene ligand has a structure of:

10. The catalyst composition of claim 1 , wherein the 1-octene catalyst comprises a ligand having the structure of:

and the 1-hexene catalyst comprises ligand having the structure of:

11. A process to produce a composition comprising 1-hexene and 1-octene from olefins, the process comprising contacting a reactant stream comprising ethylene with a solution comprising the catalyst composition of claim 1 under conditions sufficient to oligomerize the ethylene and produce an oligomer composition comprising the 1-hexene and 1-octene.

12. The process of claim 11 , wherein a weight ratio of the 1-hexene catalyst to 1-octene catalyst is from 10:1 to 1:10.

13. The process of claim 11 , wherein the weight ratio of 1-hexene to 1-octene in the oligomer composition is greater than 0.5:1.

14. The process of claim 11 , wherein the weight ratio of 1-hexene catalyst to 1-octene catalyst is about 1:1, and the weight ratio of 1-hexene to 1-octene in the oligomer composition is at least 2.5:1.

15. The process of claim 11 , wherein the weight ratio of 1-hexene catalyst to 1-octene catalyst is about 1:2.3, and the weight ratio of 1-hexene to 1-octene in the oligomer composition is at least 1.5:1.17.

16. The process of claim 11 , wherein the weight ratio of 1-hexene catalyst to 1-octene catalyst is about 1:4, and the weight ratio of 1-hexene to 1-octene in the oligomer composition is 1:1 or greater; or the weight ratio of 1-hexene catalyst to 1-octene catalyst is about 1:8, and the weight ratio of 1-hexene to 1-octene in the oligomer composition is greater than 1:1.3.

17. The catalyst composition of claim 2 , wherein the chromium (III) species is selected from the group consisting of chromium (III) acetylacetonate, Cr(2,2,6,6,-tetramethyl-3,5-heptadionate) 3 , chromium (III) 2-ethylhexanoate, chromium trichloride tris-tetrahydrofuran, (benzene) tricarbonyl chromium, chromium (III) octanoate, chromium hexacarbonyl, and chromium (III) naphthenate.

18. The catalyst composition of claim 2 , wherein the activator or co-catalyst is a methylaluminoxane compound.

19. The catalyst composition of claim 18 , wherein the methylaluminoxane compound is a methyl iso-butyl aluminum oxide compound.

20. The catalyst composition of claim 4 , wherein Ar 1 and Ar 2 are phenyl.

21. The catalyst composition of claim 7 , wherein R 1 and R 2 are each a cyclohexyl group.

22. The catalyst composition of claim 1 , wherein the weight ratio of 1-hexene catalyst to 1-octene catalyst is about 1:1 to about 1:9.

Assignees

• Sabic Global Technologies Bv

Inventors

• Al-Dajane Maher
• Al-Nezari Abdulaziz
• Korobkov Ilia
• Albahily Khalid

Classifications

• C07F9/5027

  Polyphosphines · CPC title

• B01J2531/62

  Chromium · CPC title

• B01J2231/20

  Olefin oligomerisation or telomerisation · CPC title

• Y02P20/52

  using catalysts, e.g. selective catalysts · CPC title

• C07C2531/24

  Phosphines · CPC title